From Outreach to Paid: Manny Medina on AI agents, SaaS monetisation, and building for the future

SaaStock Founder and CEO Alex Theuma speaks with Manny Medina, Co-founder and CEO of Paid (and former Founder and CEO of Outreach), about how AI is reshaping SaaS monetisation and the future of work. Manny shares his journey from scaling Outreach to $250M ARR to launching Paid, an AI-native platform built to help SaaS businesses move beyond seat-based pricing models. He explains why legacy systems are holding founders back, how to stay truly customer-obsessed, and why over half of every org chart could soon be filled by AI agents. Tune in to hear more about:: - Building a new monetisation stack for the AI era. - Why “seat-based pricing” is becoming obsolete. - The importance of in-person customer relationships. - Avoiding operational debt as you scale from startup to $100M+ ARR. Guest links: LinkedIn - https://www.linkedin.com/in/medinism/ Website - https://paid.ai/       Check out the other ways SaaStock is helping SaaS founders move their business forward:  🇮🇪 SaaStock Europe: 14-15 October 2025 | Dublin, Ireland Book tickets: https://saastock-europe.com/tickets/ 🇺🇸 SaaStock USA 2025: April 2026 | Austin, Texas Book tickets: https://saastock-usa.com/ 🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/) 🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)